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Original Articles

Efficient and Stereo-Selective Syntheses of Three Stereoisomers of the Sex Pheromone of the Cowpea Weevil, Callosobruchus maculatus

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Pages 2720-2724 | Received 17 May 2007, Accepted 19 Jul 2007, Published online: 22 May 2014

  • 1) Southgate, B. J., Biology of the Bruchidae. Ann. Rev. Entomol., 24, 449–473 (1979).
  • 2) Nojima, S., Shimomura, K., Honda, H., Yamamoto, I., and Ohsawa, K., Contact sex pheromone components of the cowpea weevil, Callosobruchus maculatus. J. Chem. Ecol., DOI 10.1007/s10886-007-9266-5.
  • 3) Nakai, T., Yajima, A., Akasaka, K., Kaihoku, T., Ohtaki, M., Nukada, T., Ohrui, H., and Yabuta, G., Synthesis of the four stereoisomers of 2,6-dimethyloctane-1,8-dioic acid, a component of the copulation release pheromone of the cowpea weevil, Callosobruchus maculatus. Biosci. Biotechnol. Biochem., 69, 2401–2408 (2005).
  • 4) Yajima, A., Akasaka, K., Nakai, T., Maehara, H., Ohrui, H., Nukada, T., and Yabuta, G., Direct determination of the stereoisomer constitution by 2D-HPLC and stereochemistry-pheromone activity relationship of the copulation release pheromone of the cowpea weevil, Callosobruchus maculatus. Tetrahedron, 62, 4590–4596 (2006).
  • 5) Rup, P. J., and Sharma, S. P., Behavioural response of males and females of Callosobruchus maculatus to sex pheromone. Indian J. Ecol., 5, 72–76 (1978).
  • 6) Qi, Y. T., and Burkholder, W. E., Sex pheromone biology and behavior of the cowpea weevil Callosobruchus maculatus (Coleoptera: Bruchidae). J. Chem. Ecol., 8, 527–534 (1982).
  • 7) Ramaswamy, S. B., Shu, S., Monroe, W. A., and Mbata, G. N., Ultrastructure and potential role of integumentary glandular cells in adult male and female Callosobruchus subinnotatus (Pic) and C. maculatus (Fabricius) (Coleoptera: Bruchidae). Int. J. Insect Morphol. Embryol., 24, 51–61 (1995).
  • 8) Phillips, T. W., Phillips, J. K., Webster, F. X., Tang, R., and Burkholder, W. E., Identification of sex pheromones from cowpea weevil, Callosobruchus maculatus, and related studies with C. analis (Coleoptera: Bruchidae). J. Chem. Ecol., 22, 2233–2249 (1996).
  • 9) Fujisawa, T., Sato, T., Gotoh, Y., Kawashima, M., and Kawara, T., Reaction of diketene with Grignard reagents in the presence of cobalt catalyst. A convenient method for the synthesis of 3-methylenealkanoic acids leading to terpenoids. Bull. Chem. Soc. Jpn., 55, 3555–3559 (1982).
  • 10) Yong, K. H., Lotoski, J. A., and Chong, J. M., Studies on the alkylation of 3-methyl-3-buten-1-ol dianion: an efficient synthesis of 3-methylene-1-alkanols including a San Jose scale sex pheromone. J. Org. Chem., 66, 8248–8251 (2001).
  • 11) Dess, D. B., and Martin, J. C., Readily accessible 12-I-5 oxidant for the conversion of primary and secondary alcohols to aldehydes and ketones. J. Org. Chem., 48, 4155–4156 (1983).
  • 12) Bal, B. S., Childers, Jr., W. E., and Pinnick, H. W., Oxidation of α,β-unsaturated aldehydes. Tetrahedron, 37, 2091–2096 (1981).
  • 13) Rand, C. L., Van Horn, D. E., Moore, M. W., and Negishi, E., A versatile and selective route to difunctional trisubstituted (E)-alkene synthons via zirconium-catalyzed carboalumination of alkynes. J. Org. Chem., 46, 4093–4096 (1981).
  • 14) Ma, S., and Negishi, E., Anti-carbometalation of homopropargyl alcohols and their higher homologues via non-chelation-controlled syn-carbometalation and chelation-controlled isomerization. J. Org. Chem., 62, 784–785 (1997).
  • 15) Negishi, E., transition metal-catalyzed organometallic reactions that have revolutionized organic synthesis. Bull. Chem. Soc. Jpn., 80, 233–257 (2007).
  • 16) Hayashi, T., Konishi, M., and Kumada, M., Dichloro[1,1′-bis(diphenylphosphinoferrocene]palladium(II): an effective catalyst for cross-coupling reaction of a secondary alkyl Grignard reagent with organic halides. Tetrahedron Lett., 1871–1874 (1979).
  • 17) Pinsker, O. A., Tsiklauri, P. G., and Grigoéva, N. Y., Highly stereoselective synthesis of a sex pheromone of the dry bean beetle Callosobruchus analis. Russ. Chem. Bull., 48, 1373–1375 (1999).
  • 18) Grigoéva, N. Y., Tsiklauri, P. G., and Pinsker, O. A., An alternative synthesis of a sex pheromone of the dry bean beetle Callosobruchus analis. Russ. Chem. Bull., 48, 1376–1379 (1999).
  • 19) Abarbri, M., Thibonnet, J., Parrain, J., and Duchêne, A., Palladium-catalyzed cross-coupling of iodovinylic acids with organometallic reagents. Selective synthesis of 3,3-disubstituted prop-2-enoic acids. Synthesis, 543–551 (2002).
  • 20) Breitfelder, S., Schuemacher, A. C., Rölle, T., and Kikuchi, M., Hoffmann, R. W., Synthesis of pederic acid and related model studies. Helv. Chim. Acta, 87, 1202–1213 (2004).
  • 21) Abe, Y., Goto, H., Sato, M., and Kato, T., Studies on ketene and its derivatives. CXV. Reaction of diketene with organometallics in the presence of the nickel- or palladium-phosphine complex. Chem. Pharm. Bull., 31, 1108–1111 (1983).
  • 22) Abe, Y., Sato, M., Goto, H., Sugawara, R., Takahashi, E., and Kato, T., Studies on ketene and its derivatives. CXVIII. Nickel- or palladium-catalyzed reaction of diketene with organometallics. Synthesis of 3-substituted 3-butenoic acids. Chem. Pharm. Bull., 31, 4346–4354 (1983).
  • 23) Bunce, R. A., Smith, C. L., and Lewis, J. R., Tetrahydro-1,5-benzoxazepines and tetrahydro-1H-1,5-benzodiazepines by a tandem reduction-reductive amination reaction. J. Heterocyclic Chem., 41, 963–970 (2004).
  • 24) Vasil’ev, A. A., Kryshtal, G. V., and Serebryakov, E. P., A convenient protocol for the stereocontrolled synthesis of olefins with a homoallylic type of functionality. Mendeleev Commun., 41–42 (1995).
  • 25) Vasil’ev, A. A., Vlasyuk, A. L., Gamalevich, G. D., and Serebryakov, E. P., A versatile convenient protocol for the stereocontrolled synthesis of olefinic insect pheromones. Bioorg. Med. Chem., 4, 389–400 (1996).
  • 26) Shu, S., Koepnick, W. E., Mbata, G. N., Cork, A., and Ramaswamy, S. B., Sex pheromone production in Callosobruchus maculatus (Coleoptera: Bruchidae): electroantennographic and behavioral responses. J. Stored Prod. Res., 32, 21–30 (1996).
  • 27) Cork, A., Hall, D. R., Blaney, W. M., and Simmonds, M. S. J., Identification of a component of the female sex pheromone of Callosobruchus analis (Coreoptera: Bruchidae). Tetrahedron Lett., 32, 129–132 (1991).
  • 28) Shu, S., Mbata, G. N., Cork, A., and Ramaswamy, S. B., Sex pheromone of Callosobruchus subinnotatus. J. Chem. Ecol., 25, 2715–2727 (1999).

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